American country singer, guitarist, and songwriter One of the founders of country music’s outlaw movement, Jennings gave voice to the sorrowful side of the genre’s lyrical content.
Born: June 15, 1937; Littlefield, Texas
Died: February 13, 2002; Chandler, Arizona
Waylon Arnold Jennings was just twelve years old when he began working at a radio station in Littlefield as a country-music deejay. At fourteen, Jennings quit school, spent some time picking cotton, and then settled in Lubbock, about forty miles from his hometown. In 1954 Jennings began deejaying again at KLLL in Lubbock. While working at the radio station, he met up-and-coming artist Buddy Holly, who would go on to become an acclaimed rock singer and guitarist. The two became close friends, and Holly asked the nineteen-year-old Jennings to join his band, the Crickets, as bass player. Jennings later admitted that he had been playing the instrument for only a few weeks when he began touring with Holly. During the tour, Holly chartered a plane for his bandmates one night in February, 1959. Jennings gave up his seat to J. P. Richardson, also known as the Big Bopper,whowas suffering from a cold.
That split-second decision affected the rest of Jennings’s life. In what became known as “the day the music died,” the plane crashed in Iowa, killing Holly, Richardson, and Ritchie Valens (known for his hit “La Bamba”). Jennings harbored guilt over the accident because he had joked to Holly that he hoped his plane would crash. After he found little success in Texas and Arizona, Jennings moved to Nashville, Tennessee, in the mid-1960’s, and he became roommates with Johnny Cash. The two formed a lifelong friendship, cemented at the time by their substance abuse. In 1965, with the help of Bobby Bare and Chet Atkins, Jennings signed a contract with RCA Records. Jennings appreciated the artistic freedom his producer Atkins allowed him, as opposed to the demands placed by the rest of the country-music industry to look, act, and sing a certain way. Jennings also found a friend in Willie Nelson, who, like Jennings, stubbornly asserted artistic control against the Nashville establishment. The two quickly became known as “outlaws.” Jennings had been married three times before he was thirty, but in October, 1969, he married country musician Jessi Colter, in a lasting union. The Cash- Jennings relationship is depicted in the motion picture Walk the Line (2005), with Jennings and Colter’s son Shooter playing Waylon.
Substance abuse problems, particularly his use of cocaine, plagued Jennings throughout the height of his popularity in the 1970’s, and it would take until the mid-1980’s until he was free from drugs. By 1989 Jennings, who had dropped out of school in the tenth grade, had received his GED, a high school equivalency diploma. He wanted to finish high school to impress upon his ten-year-old son the importance of education. Jennings died from complications related to diabetes on February 13, 2002, in Chandler, Arizona. The Music Early Works. While on Holly’s Winter Dance Party Tour, Jennings’s star as a bassist began to rise, prompting him to form his own band, Jennings and the Waylors, in Phoenix, Arizona, in late 1960 after Holly’s tragic death. Three years later, he moved again, to Los Angeles, signing a contract with Herb Alpert’s A&M Records. The label wanted him to make a pop album, which Jennings refused to do. His first single, “Sing the Girl a Song, Bill,” and his album were failures. Folk-Country. With this first album from RCA Records, marking his first attempt at the Nashville sound, Jennings began scoring hits in the world of country music, starting with “Stop the World (And Let Me Off),” which made the Top 40.
He continued with this success, releasing several albums that featured such hits as “Walk on out of My Mind,” “I Got You,” “Only Daddy That’ll Walk the Line,” and “Yours Love” – all Top 10 hits in 1968. After these successes, Jennings was even more determined to do things his way. He was constantly in conflict with the music establishment in Nashville. Whenhe beganworking with staff producer Danny Davis, after Atkins, Jennings said that he was being bullied, and he pointed a pistol at Davis in the studio. Wanted! The Outlaws. Jennings’s next big move solidified his reputation as an outlaw and helped him to become a mainstream artist. The album Wanted! The Outlaws focused on Jennings but his collaborators were Willie Nelson, Tompall Glaser, and Colter. It became the first country record to be certified platinum, and it peaked at number one on the pop charts. Wanted! The Outlaws catapulted Jennings into pop music stardom, and it certainly boosted his career as a country musician. Jennings continued his solo success with Dreaming My Dreams, which was the first of his many numberone albums. He was also voted Best Male Vocalist of the Year at the Country Music Awards in 1975, and his work with Nelson on Wanted! The Outlaws earned them the Country Music Awards Duo of the Year in 1977. Waylon and Willie.
After the success of Wanted! The Outlaws, the duo teamed up for Waylon and Willie, an album that would link their names for a generation of country fans. The two worked together on many projects throughout the years, but it all started with the crossover hits “Luckenbach, Texas” and “Mammas Don’t Let Your Babies Grow up to Be Cowboys” – which won a 1978 Grammy for Best Country Vocal Performance by a Duo or Group. The Dukes of Hazzard. Throughout the 1980’s, Jennings maintained his musical popularity. He had several number-one singles, such as “Amanda,” “I Ain’t Living Long Like This,” “Lucille (You Won’t Do Your Daddy’s Will),” and “I’ve Always Been Crazy.” Jennings was also a large part of the television comedy The Dukes of Hazzard. Jennings wrote and sang the show’s theme song, and he did the offscreen narration, which introduced his voice to millions of viewers. Highwayman. In 1985 Jennings teamed up with friends Nelson, Cash, and Kris Kristofferson to record Highwayman. The Columbia Records album went gold, and the title track was a number-one single and a huge hit for all four artists. At the same time, Jennings’s solo career underwent a change whenhe leftRCAin 1986 and signed a contract with MCA Nashville Records, in an effort to revitalize his career after kicking his addiction.
He had a few number-one singles with MCA, including “Rose in Paradise.” Jennings switched labels again in 1990 to Epic Records,where he scored twomore Top 40 hits with “Wrong” and “The Eagle.” Closing in on the Fire. Although Jennings continued to work throughout the 1990’s, most of his solowork and compilations – includingmorework with the Highwaymen and Nelson – did not reach the success he had experienced in the 1970’s and the 1980’s. Jennings was an accomplished performer, and his tours drew huge crowds. In 1996 Jennings released his autobiography, Waylon. Throughout the late 1990’s, Jennings’s work slowed down as his health deteriorated because of heart disease and diabetes. Jennings stopped touring in 1997, but the following year he released the well-received album Closing in on the Fire, which featured Travis Tritt, Sting, Sheryl Crow, Mick Jagger, and Colter. This was Jennings’s last studio album. Musical Legacy A stunningly prolific artist, Jennings released seventy-two albums throughout his career, all while battling the conservative tendencies of the Nashville music establishment. A rebel to the end, Jennings refused to attend the ceremony when he was inducted into the Country Music Hall of Fame in 2001, believing that artists should not compete against each other. In spite of his aversion to awards ceremonies, he received two Grammy Awards, for Best Country Performance by a Duo, and four Country Music Awards, for Album of the Year, Single of the Year, Vocal Duo of the Year, and Male Vocalist of the Year.